DE2236778C3 - 2 β, 3 β, 5 β, 11 α, 14 α, 20 R, 22R-Heptahydroxy- 5 β- cholest-7-en-6-on, seine Gewinnung und seine Verwendung als Insektizid - Google Patents
2 β, 3 β, 5 β, 11 α, 14 α, 20 R, 22R-Heptahydroxy- 5 β- cholest-7-en-6-on, seine Gewinnung und seine Verwendung als InsektizidInfo
- Publication number
- DE2236778C3 DE2236778C3 DE2236778A DE2236778A DE2236778C3 DE 2236778 C3 DE2236778 C3 DE 2236778C3 DE 2236778 A DE2236778 A DE 2236778A DE 2236778 A DE2236778 A DE 2236778A DE 2236778 C3 DE2236778 C3 DE 2236778C3
- Authority
- DE
- Germany
- Prior art keywords
- methanol
- muristeron
- residue
- insecticide
- production
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 239000002917 insecticide Substances 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title description 4
- 229930187267 Muristeron Natural products 0.000 claims description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- LRJUYAVTHIEHAI-LHBNDURVSA-N Muristerone Chemical compound C1[C@@H](O)[C@@H](O)C[C@]2(C)[C@@H]([C@H](O)C[C@@]3([C@@H]([C@@](C)(O)[C@H](O)CCC(C)C)CC[C@]33O)C)C3=CC(=O)[C@@]21O LRJUYAVTHIEHAI-LHBNDURVSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- YXPVYQIMXPYFSF-UHFFFAOYSA-N Makisterone A Natural products CC(C)C(C)(O)CC(O)C(C)(O)C1CCC2(O)C3=CC(=O)C4CC(O)C(O)CC4(C)C3CCC12C YXPVYQIMXPYFSF-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 230000001418 larval effect Effects 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 241000238631 Hexapoda Species 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 150000003431 steroids Chemical class 0.000 description 6
- IJRBORPEVKCEQD-JMQWOFAPSA-N Makisterone A Chemical compound C1[C@@H](O)[C@@H](O)C[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@@](C)(O)[C@H](O)C[C@@H](C)C(C)(C)O)CC[C@]33O)C)C3=CC(=O)[C@@H]21 IJRBORPEVKCEQD-JMQWOFAPSA-N 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- NKDFYOWSKOHCCO-YPVLXUMRSA-N 20-hydroxyecdysone Chemical compound C1[C@@H](O)[C@@H](O)C[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@@](C)(O)[C@H](O)CCC(C)(O)C)CC[C@]33O)C)C3=CC(=O)[C@@H]21 NKDFYOWSKOHCCO-YPVLXUMRSA-N 0.000 description 4
- UPEZCKBFRMILAV-UHFFFAOYSA-N alpha-Ecdysone Natural products C1C(O)C(O)CC2(C)C(CCC3(C(C(C(O)CCC(C)(C)O)C)CCC33O)C)C3=CC(=O)C21 UPEZCKBFRMILAV-UHFFFAOYSA-N 0.000 description 4
- NKDFYOWSKOHCCO-UHFFFAOYSA-N beta-ecdysone Natural products C1C(O)C(O)CC2(C)C(CCC3(C(C(C)(O)C(O)CCC(C)(O)C)CCC33O)C)C3=CC(=O)C21 NKDFYOWSKOHCCO-UHFFFAOYSA-N 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 230000000749 insecticidal effect Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- SGNLNHWVOICCOZ-UHFFFAOYSA-N Crustecdyson Natural products CC(O)C1(CCC2(O)C3=CC(=O)C4CC(O)C(O)CC4(C)C3CCC12C)C(O)CCC(C)(C)O SGNLNHWVOICCOZ-UHFFFAOYSA-N 0.000 description 3
- 229930183445 Makisteron Natural products 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- UPEZCKBFRMILAV-JNEQICEOSA-N Ecdysone Natural products O=C1[C@H]2[C@@](C)([C@@H]3C([C@@]4(O)[C@@](C)([C@H]([C@H]([C@@H](O)CCC(O)(C)C)C)CC4)CC3)=C1)C[C@H](O)[C@H](O)C2 UPEZCKBFRMILAV-JNEQICEOSA-N 0.000 description 2
- 240000007218 Ipomoea hederacea Species 0.000 description 2
- 241000255777 Lepidoptera Species 0.000 description 2
- XZPRTSYANZNFAS-UHFFFAOYSA-N [CH2-]C(C)=O.CC(O)=O.CC(O)=O Chemical compound [CH2-]C(C)=O.CC(O)=O.CC(O)=O XZPRTSYANZNFAS-UHFFFAOYSA-N 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 2
- UPEZCKBFRMILAV-JMZLNJERSA-N ecdysone Chemical compound C1[C@@H](O)[C@@H](O)C[C@]2(C)[C@@H](CC[C@@]3([C@@H]([C@@H]([C@H](O)CCC(C)(C)O)C)CC[C@]33O)C)C3=CC(=O)[C@@H]21 UPEZCKBFRMILAV-JMZLNJERSA-N 0.000 description 2
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000004744 fabric Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000255789 Bombyx mori Species 0.000 description 1
- 241000217446 Calystegia sepium Species 0.000 description 1
- 208000034656 Contusions Diseases 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000207783 Ipomoea Species 0.000 description 1
- 235000021506 Ipomoea Nutrition 0.000 description 1
- 241000598138 Ipomoea muricata Species 0.000 description 1
- 235000008708 Morus alba Nutrition 0.000 description 1
- 240000000249 Morus alba Species 0.000 description 1
- OCPPFMRNHHVVLW-UHFFFAOYSA-N [CH2-]C(C)=O.CC(O)=O.CC(O)=O.CC(O)=O Chemical compound [CH2-]C(C)=O.CC(O)=O.CC(O)=O.CC(O)=O OCPPFMRNHHVVLW-UHFFFAOYSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- FQRDUCUXACEVCK-UHFFFAOYSA-N benzene;dichloromethane;methanol Chemical compound OC.ClCCl.C1=CC=CC=C1 FQRDUCUXACEVCK-UHFFFAOYSA-N 0.000 description 1
- 208000034526 bruise Diseases 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000002428 insect molting hormone Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT780571 | 1971-07-29 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2236778A1 DE2236778A1 (de) | 1973-02-08 |
| DE2236778B2 DE2236778B2 (de) | 1981-04-09 |
| DE2236778C3 true DE2236778C3 (de) | 1982-03-25 |
Family
ID=11125374
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2236778A Expired DE2236778C3 (de) | 1971-07-29 | 1972-07-26 | 2 β, 3 β, 5 β, 11 α, 14 α, 20 R, 22R-Heptahydroxy- 5 β- cholest-7-en-6-on, seine Gewinnung und seine Verwendung als Insektizid |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3795686A (https=) |
| AU (1) | AU4503772A (https=) |
| DE (1) | DE2236778C3 (https=) |
| FR (1) | FR2147750A5 (https=) |
| GB (1) | GB1397431A (https=) |
| ZA (1) | ZA725157B (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1118225B (it) * | 1977-08-12 | 1986-02-24 | Simes | Procedimento per l'ottenimento di steroidi poliossidrilati,lisergolo ed alcaloidi ergolici |
| HUP9904616A3 (en) | 1996-12-20 | 2001-02-28 | Novo Nordisk As | Meiosis regulating cholestane-derivatives |
-
1972
- 1972-07-25 ZA ZA725157A patent/ZA725157B/xx unknown
- 1972-07-26 DE DE2236778A patent/DE2236778C3/de not_active Expired
- 1972-07-26 US US00275169A patent/US3795686A/en not_active Expired - Lifetime
- 1972-07-26 GB GB3498972A patent/GB1397431A/en not_active Expired
- 1972-07-27 AU AU45037/72A patent/AU4503772A/en not_active Expired
- 1972-07-28 FR FR7227419A patent/FR2147750A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2147750A5 (https=) | 1973-03-09 |
| DE2236778B2 (de) | 1981-04-09 |
| AU4503772A (en) | 1974-01-31 |
| US3795686A (en) | 1974-03-05 |
| DE2236778A1 (de) | 1973-02-08 |
| ZA725157B (en) | 1973-04-25 |
| GB1397431A (en) | 1975-06-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |